Ms. Mystery

07.30.124:45 AM ET

Who Is Lauryn Hill? The Singer After the Fugees, Seclusion, Tax Issues

Years after the Fugees’ breakup, a seminal solo album, a retreat from music, and a chaotic return, the singer is back in the news after pleading guilty to tax evasion. Friends tell Allison Samuels how Ms. Hill got here.

Take a peek at singer Lauryn Hill’s touring schedule, and you’ll see she’s quite the busy lady. The former lead singer of the Fugees has booked concert dates around the U.S. and in several other countries over the next few months, and she performed just last weekend in Russia. And though in recent years tales of Hill showing up hours late or even canceling planned performances have abounded, there’s one upcoming date she is not likely to miss. At a court hearing in November, she will learn whether she will be sentenced to up to three years in jail for tax evasion.

On June 29, as Hill stood quietly in federal court in Newark, N.J., and pleaded guilty to not paying her taxes for three years, many of her friends, fans, and associates wondered how the 37-year-old singer, whose seminal 1998 solo album, The Miseducation of Lauryn Hill, sold 18 million copies worldwide and defined an era of music, could have ended up this way. What went so wrong that one of the most fearless female forces in all of hip-hop could find herself at the mercy of a court—one that also has ordered her to undergo mental-health counseling?

From all accounts, the answers are as plentiful as they are complicated and as disappointing as they are sad.

The second child of a high-school teacher and a computer programmer, Hill grew up in Orange, N.J., listening to the old ’60s Motown records. In between attending bar mitzvahs of childhood friends like Zach Braff, a teenage Hill also managed to win Amateur Night at Showtime at the Apollo singing a Smokey Robinson song. Not long after, she appeared as a student singing her heart out in the 1993 film Sister Act 2 and accepted an invitation from a school friend named Praskazrel “Pras” Michel to become a member of his new band, which also would include his cousin Wyclef Jean. Hill used the comfort she found in the group structure to turn her love of writing prose and poetry into hypnotic rap rhymes that set the Fugees worlds apart from other acts on the ’90s hip-hop landscape. Songs like “Killing Me Softly,” “Ready or Not,” and “Fu-Gee-La” dominated radio stations for months and catapulted the Fugees to international fame.

But while there were three members in the group, it was Hill who ended up stealing the spotlight.

“The first time I saw Lauryn Hill, I said, ‘Who is that pretty chocolate girl with such a great voice?’” remembers Mary J. Blige, who worked with Hill on her solo album. “You couldn’t take your eyes off her because she was ‘that’ girl.”

Hill’s striking good looks, smooth mahogany skin, doe eyes, and short Afro were a major departure from the female artists who topped the charts in the mid-’90s. Add to the mix her sultry voice and penchant for body-skimming outfits on her slender frame, and a completely different type of sex symbol was born.

Both the music and movie world fell in love with “L Boogie,” as she was called, and at the height of her career she was said to have turned down roles in The Matrix, Charlie’s Angels, and The Bourne Identity. And she paved the way for singers such as Alicia Keys, Jill Scott, and Norah Jones.

Hill’s breakout fame, however, didn’t elicit warm feelings from her band mates in the Fugees. The tensions among the three were heightened further by Hill’s “complicated” romantic relationship with Jean, according to friends. The two dated on and off during the early years of the group’s development and success.

“The pressure of being so famous and to live up to all the expectations of her was just too much.”

“It wasn’t the best relationship for either one of them,” said a former employee of Hill’s. “She was young and talented, with everyone coming at her wanting to give her everything. Wyclef wanted control over that and her, in some ways, and that always comes to a negative end.”

The relationship fizzled, but that was only the beginning of Hill’s woes. Her world would be changed forever when she announced plans for her first solo album. Though Jean had success with his own solo effort just the year before, he reportedly was furious about Hill’s decision to separate from the group, which disbanded in 1997. And while Hill contributed verses and production to his 1997 album, The Carnival, Jean reportedly initially refused to help Hill in any way on her new album. Around the same time, she became romantically involved with Rohan Marley, son of reggae legend Bob Marley.

“She went from one unhealthy relationship to another very quickly,” said her former employee. “But that’s what happens when you really want and really need to be loved and in love. That’s how Lauryn was.”

That need for love and the consequences provided a powerful lyrical background for The Miseducation of Lauryn Hill. Upon its release, the landmark album quickly became the brightest star in the neo-soul atmosphere, selling nearly 500,000 copies in its first week of release, breaking the sales record for a female artist. Hill mixed genres from track to track, effortlessly flowing from hip-hop to gospel to reggae while using her lyrical prowess to explore heartache, doomed love, and the impending birth of her first child, Zion. The critical acclaim for Miseducation was equaled only by the 10 Grammy nominations she received in 1999. Hill walked away with five awards that night, including Best New Artist and the coveted Album of the Year.

“That album still rates as one of the best of all time in the world of hip-hop,” said Kim Osorio, editor in chief of The Source magazine. “Lauryn is still at the top of the list of the best lyricists today. All women related to that album and what she was saying in it. But guys loved it too. That’s rare for a female hip-hop artist.”

But as Hill began to grace the covers of Esquire, Teen People, and Time, her success was marred by a lawsuit that claimed she had failed to give proper credit to New Ark, a group of hip-hop producers and writers who alleged they co-wrote and -produced several of the album’s songs. During the recording of Miseducation, New Ark claimed, they asked for contracts and documentation, but were allegedly told by Hill, “We all love each other. This isn’t about documents. This is blessed.”

Apparently love had nothing to do with it, and New Ark filed a 50-page lawsuit against Hill and her record company, Sony, asking for partial writing credits and monetary reimbursement. The case was eventually settled out of court in 2001, for a reported $5 million. But money wasn’t all that was lost for Hill, who reportedly took the lawsuit hard. She accused the producers of being mean-spirited and of taking advantage of her success.

“It’s unfortunate because it wasn’t Lauryn’s idea to say she’d done it all. It was the record company that was big on saying she’d done all the writing, producing, and everything else,” said a friend of Hill’s. “They wanted her to have title to somehow make her bigger than she was. They do that with a lot of artists, but it backfired that time, and Lauryn got caught in the middle. She was very angry about it and stayed angry for a while.”

Back-to-back pregnancies in 1997 and 1998 further complicated Hill’s emotional state, along with her growing desire to stay home with her family instead of touring. From 1998 to 1999, Hill earned an estimated $25 million from record sales and concerts.

Still, her anger over the lawsuit persisted, as did the strain of preparing a follow-up album worthy of comparison to Miseducation. In 2000 Hill began to shun the spotlight completely. She began to explore her creativity in other ways, such as clothing design and writing a script about the life of Bob Marley. She also began to speak about herself in the third person.

“People need to understand that the Lauryn Hill they were exposed to in the beginning was all that was allowed in that arena at the time,” Hill said in a 2000 interview. “I had to step away for the sake of the machine. I was being way too compromised. I felt uncomfortable having to smile in someone’s face when I really didn’t like them or know them well enough to like.”

She added: “I had to confront my fears and master my every demonic thought about inferiority, insecurity, or the fear of being black, young, and gifted in this Western culture.”

Hill gave birth to another child in 2002 and felt sure the record company was trying to control her. She fired her management team and began attending Bible class five days a week. At the same time, she stopped giving interviews, watching television, and listening to music. Friends say Hill also began a close relationship with a “spiritual adviser” named Brother Anthony, who would guide her every move for years. He also, those friends told The Daily Beast, encouraged Hill’s more eccentric behavior.

That behavior included lashing out at the Catholic Church during a benefit concert she took part in at the Vatican in 2003. She called on church leaders to repent, supposedly for the molestation of young boys in the United States, and instructed the crowd to seek blessings from God and not man. Her performance was cut from the television broadcast. Later on, as she resumed touring, she began appearing at shows more three hours late and often arrived with orange-colored hair and clownish makeup. She reportedly instructed those who worked for her at Sony and members of the Fugees to address her as “Ms. Hill” and toyed with changing her name to “Empress.”

“I think something just broke at that time for Lauryn,” said her close friend. “The pressure of being so famous and to live up to all the expectations of her was just too much. Not to mention the pressure of having several young children back to back over the course of only five or six years. She and Rohan had a host of relationship problems that didn’t help much either.”

Marley and Hill never married, and rumors ran rampant that he cheated on her throughout their relationship.

No one knows when exactly the longtime couple split, but Marley is currently engaged to Brazilian model Isabeli Fontana. He has denied being the father of Hill’s sixth child, born last year. Neither event has been helpful to Hill’s state of mind, say friends.

The last few years shellshocked Hill, say friends, especially the years she is accused of not paying taxes. Court papers show she failed to file tax returns from 2005 to 2007. She faces a maximum one-year sentence on each of the three counts.

After the IRS brought charges against Hill, she took to her Tumblr to post a rambling statement that lashed out at pop culture’s “climate of hostility, false entitlement, manipulation, racial prejudice, sexism and ageism.” She also said she failed to pay taxes in order to guarantee the safety and well-being of herself and her family. Hill stressed that she had not spent extravagantly, and while she resided for years in hotels in and around Miami, court records now indicate she lives at her mother’s home in New Jersey.

Despite Hill’s defiant stance online, her attorney Nathan Hockman insists the singer will pay back the almost $2 million she owes by her November sentencing date in hopes of receiving a reduced sentence. The initial court date was set for October, but was delayed one month to allow Hill time to repay the full amount.

“By admitting her guilt, accepting full responsibility for her actions, and paying the IRS, we hope that Ms. Hill will receive a fair and balanced sentence of probation,” Hockman told The Daily Beast.

Hockman added that the court-ordered mental-health counseling is essentially family counseling that involves the entire Hill family. “The court directed Ms. Hill to continue family counseling she had begun voluntarily started before her bail began,” he said. He added that the singer is fully capable of continuing a lucrative musical career that won’t be affected by recent events.

But fans who have watched performances in recent months by Hill, who has not released an album since MTV Unplugged 2.0 in 2002, say they are not so sure she can return to her former pedestal among hip-hop fans. They say they witnessed a woman on stage struggling to keep it together and seemingly in search of where she now fits in the musical landscape.

“I saw her a few months ago in New York, and it was OK, but not what I was expecting,” said Alex Turner, 32, of Harlem. “Miseducation was the soundtrack of my life, literally, and she barely sang one from song from that album, and when she did it, I barely recognized it. It was kind of showroom, cocktail-dinner music. Not the music of the ‘L Boogie’ I fell in love with in the ’90s. I’m not sure who that woman was on stage. I’m not sure she knew either.”